Two paths are proposed by which 25-hydroxycholesterol might be efficiently prepared from cholesterol. A third path is proposed by which 25-hydroxycholesterol might be made from either cholesterol or sitosterol. The importance of 25-hydrocholesterol is documented. It is the objective of current pharmaceutical research. It acts to increase the rate of calcium turnover and could become important clinically. The three proposed paths utilize methods of remote hydroxylation and remote functionalization. This is an area in which we have expertise. One path uses a new and efficient method of protecting the 5,6 double bond via the 6 beta-acetamide derivative. This method is a recent discovery of our group.